N-hydroxy-N-1-(5-methylthien-2-yl)ethyl urea | 120110-41-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: N-hydroxy-N-1-(5-methylthien-2-yl)ethyl urea
• 英文别名: N-hydroxy-N-[1-(5-methylthien-2-yl)ethyl]urea；1-hydroxy-1-[1-(5-methylthiophen-2-yl)ethyl]urea
• CAS: 120110-41-0
• 化学式: C₈H₁₂N₂O₂S
• 分子量: 200.261
• InChiKey: KOGZKDFYLMFBKB-UHFFFAOYSA-N

物化性质

• 沸点：
  370.5±44.0 °C(Predicted)
• 密度：
  1.327±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  94.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-methyl-2-acetylthiophene oxime 在 盐酸 、 吡啶硼烷 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 2.17h， 生成 N-hydroxy-N-1-(5-methylthien-2-yl)ethyl urea
  参考文献：
  名称：

  Structure−Activity Relationships of N-Hydroxyurea 5-Lipoxygenase Inhibitors

  摘要：

  The discovery of second generation N-hydroxyurea 5-lipoxygenase inhibitors was accomplished through the development of a broad structure-activity relationship (SAR) study. This study identified requirements for improving potency and also extending duration by limiting metabolism. Potency could be maintained by the incorporation of heterocyclic templates substituted with selected lipophilic substituents. Duration of inhibition after oral administration was optimized by identification of structural features in the proximity of the N-hydroxyurea which correlated to low in vitro glucuronidation rates. Furthermore, the rate of in vitro glucuronidation was shown to be stereoselective for certain analogs. (R)-N-[3-[5-(4-Fluorophenoxy)-2-furyl]-1-methyl-2-propynyl]-N-hy- droxyurea (17c) was identified and selected for clinical development.

  DOI：

  10.1021/jm9700474

文献信息

• Urea based lipoxygenase inhibiting compounds
  申请人：Abbott Laboratories

  公开号：US05185363A1

  公开（公告）日：1993-02-09

  Substituted phenyl, naphthyl, and thienyl N-hydroxy urea compounds form a class of potent inhibitors of 5- and 12-lipoxygenase and are thus useful compounds in the treatment of inflammatory disease states where leukotrienes and other products of lipoxygenase enzyme activity are implicated.

  苯基、萘基和噻吩基N-羟基脲化合物形成了一类强效的5-和12-脂氧化酶抑制剂，因此在治疗炎症性疾病状态中，其中白三烯和其他脂氧化酶酶活性产物起作用，这些化合物是有用的。
• Addition of organolithium compounds to N-thp protected nitrone
  作者：Anwer Basha、James D. Ratajczyk、Dee W. Brooks

  DOI：10.1016/s0040-4039(00)79375-0

  日期：1991.7

  A novel synthesis of a-branched primary hydroxylamines by addition of organolithium reagents to N-THP protected nitrone is described.

  描述了一种通过向N-THP保护的硝酮中添加有机锂试剂来合成α-支链伯羟胺的新方法。
• UREA BASED LIPOXYGENASE INHIBITING COMPOUNDS
  申请人：ABBOTT LABORATORIES

  公开号：EP0588785A1

  公开（公告）日：1994-03-30
• EP0588785A4
  申请人：——

  公开号：EP0588785A4

  公开（公告）日：1991-12-30
• US5185363A
  申请人：——

  公开号：US5185363A

  公开（公告）日：1993-02-09